Camphene → exo-3,3-Dimethylbicyclo(2.2.1)heptane-2-propionic acid
Reaction equation
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.[CH:8]12[CH2:17][CH:14]([CH2:15][CH2:16]1)[C:12](=[CH2:13])[C:9]2([CH3:11])[CH3:10].C(OOC(C)(C)C)(C)(C)C.[OH-].[Na+]>>[CH3:10][C:9]1([CH3:11])[CH:8]2[CH2:17][CH:14]([CH2:15][CH2:16]2)[CH:12]1[CH2:13][CH2:6][C:5]([OH:4])=[O:7]Participants
Procedure
To refluxing acetic anhydride (1050 g., 10 moles), there is added dropwise over six hours a solution of camphene (136 g., 1 mole) and di-tert-butyl peroxide (0.1 mole, 14.6 g.). After complete addition, the mixture is heated at reflux for five hours. The cooled reaction mixture is concentrated under reduced pressure to leave a yellow-orange residual oil; 750 ml. of 2.5N NaOH is added to the residue which is then heated on the steam bath for one hour. The cooled solution is extracted once with ether, made acidic with concentrated HCl, and extracted thoroughly with ether. The dried (Na2SO4) ether extracts are concentrated under reduced pressure and the residue distilled under vacuum to give a colorless product, b.p. 141° C.-144° C./0.5 mm.
Workup
- additionAfter complete addition
- temperaturethe mixture is heated
- temperatureat reflux for five hours
- customThe cooled reaction mixture
- concentrationis concentrated under reduced pressure
- customto leave a yellow-orange residual oil
- temperatureis then heated on the steam bath for one hour
- extractionThe cooled solution is extracted once with ether
- extractionextracted thoroughly with ether
- dry with materialThe dried (Na2SO4) ether extracts
- concentrationare concentrated under reduced pressure
- distillationthe residue distilled under vacuum
- customto give a colorless product, b.p. 141° C.-144° C./0.5 mm
Sources & evidence
- ORD record
- ord-9c2966978b914690a58fa3c151d6fec9
- Source dataset
- uspto-grants-1977_09
- Patent number
- US04049559
Reaction notes
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